DE69330077T2 - Testsatz und verfahren zur bestimmung von pestiziden - Google Patents
Testsatz und verfahren zur bestimmung von pestizidenInfo
- Publication number
- DE69330077T2 DE69330077T2 DE69330077T DE69330077T DE69330077T2 DE 69330077 T2 DE69330077 T2 DE 69330077T2 DE 69330077 T DE69330077 T DE 69330077T DE 69330077 T DE69330077 T DE 69330077T DE 69330077 T2 DE69330077 T2 DE 69330077T2
- Authority
- DE
- Germany
- Prior art keywords
- luciferin
- test sample
- pesticide
- mixture
- concentration
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000575 pesticide Substances 0.000 title claims description 67
- 238000012360 testing method Methods 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 27
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical compound OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 claims description 70
- 210000004556 brain Anatomy 0.000 claims description 40
- 238000005415 bioluminescence Methods 0.000 claims description 38
- 230000029918 bioluminescence Effects 0.000 claims description 38
- CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 claims description 37
- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 claims description 37
- DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 30
- 239000000523 sample Substances 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 26
- 241000238631 Hexapoda Species 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- -1 D-luciferin ester Chemical class 0.000 claims description 20
- 108060001084 Luciferase Proteins 0.000 claims description 20
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 claims description 19
- 239000005089 Luciferase Substances 0.000 claims description 19
- 238000004020 luminiscence type Methods 0.000 claims description 17
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 238000011534 incubation Methods 0.000 claims description 12
- 241000255789 Bombyx mori Species 0.000 claims description 7
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical group CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 241000257303 Hymenoptera Species 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 241000238421 Arthropoda Species 0.000 claims description 4
- 241000257161 Calliphoridae Species 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 241000257226 Muscidae Species 0.000 claims description 3
- 239000013074 reference sample Substances 0.000 claims description 3
- 241000255925 Diptera Species 0.000 claims description 2
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 claims description 2
- LIYGYAHYXQDGEP-UHFFFAOYSA-N firefly oxyluciferin Natural products Oc1csc(n1)-c1nc2ccc(O)cc2s1 LIYGYAHYXQDGEP-UHFFFAOYSA-N 0.000 claims description 2
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 claims description 2
- JJVOROULKOMTKG-UHFFFAOYSA-N oxidized Photinus luciferin Chemical compound S1C2=CC(O)=CC=C2N=C1C1=NC(=O)CS1 JJVOROULKOMTKG-UHFFFAOYSA-N 0.000 claims description 2
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 150000002460 imidazoles Chemical class 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 241000256844 Apis mellifera Species 0.000 claims 1
- 239000005944 Chlorpyrifos Substances 0.000 claims 1
- 239000005949 Malathion Substances 0.000 claims 1
- 239000005916 Methomyl Substances 0.000 claims 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 claims 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 claims 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 claims 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 claims 1
- 229960000453 malathion Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 claims 1
- BUYMVQAILCEWRR-UHFFFAOYSA-N naled Chemical compound COP(=O)(OC)OC(Br)C(Cl)(Cl)Br BUYMVQAILCEWRR-UHFFFAOYSA-N 0.000 claims 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 claims 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 claims 1
- 238000003556 assay Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 108090000790 Enzymes Proteins 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 12
- 239000000284 extract Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 9
- 239000000872 buffer Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 241000220225 Malus Species 0.000 description 5
- 235000021016 apples Nutrition 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 230000007177 brain activity Effects 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 239000000700 radioactive tracer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- 108090000371 Esterases Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 2
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229960001456 adenosine triphosphate Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000005013 brain tissue Anatomy 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000003018 immunoassay Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000256837 Apidae Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 108090000331 Firefly luciferases Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UZMAPBJVXOGOFT-UHFFFAOYSA-N Syringetin Natural products COC1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UZMAPBJVXOGOFT-UHFFFAOYSA-N 0.000 description 1
- 239000007997 Tricine buffer Substances 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000000152 carbamate pesticide Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000000058 esterolytic effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- PULFPBAWBRMDDC-MRVPVSSYSA-N methyl (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate Chemical group COC(=O)[C@H]1CSC(=N1)c2nc3ccc(O)cc3s2 PULFPBAWBRMDDC-MRVPVSSYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- 239000003987 organophosphate pesticide Substances 0.000 description 1
- PMCVMORKVPSKHZ-UHFFFAOYSA-N oxydemeton-methyl Chemical group CCS(=O)CCSP(=O)(OC)OC PMCVMORKVPSKHZ-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000009979 protective mechanism Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/566—Immunoassay; Biospecific binding assay; Materials therefor using specific carrier or receptor proteins as ligand binding reagents where possible specific carrier or receptor proteins are classified with their target compounds
- G01N33/567—Immunoassay; Biospecific binding assay; Materials therefor using specific carrier or receptor proteins as ligand binding reagents where possible specific carrier or receptor proteins are classified with their target compounds utilising isolate of tissue or organ as binding agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/60—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances involving radioactive labelled substances
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/975—Kit
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Cell Biology (AREA)
- Zoology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Wood Science & Technology (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (17)
1. Verfahren zur Bestimmung der Konzentration von Organophosphat- und
Carbamatpestiziden in einer Testprobe, wobei das Verfahren umfasst:
a) Inkubieren einer Testprobe und eines Insektengehirnmaterials;
b) Zugeben eines 6-substituierten D-Luciferinesters zu der inkubierten Mischung,
wobei die Hydrolyse des D-Luciferinesters in der Gegenwart des Pestizids inhibiert
wird;
c) Inkubieren der Mischung aus Schritt b) zur Freisetzung von D-Luciferin;
d) Zugeben von Adenosintriphosphat und Luciferase zu der Mischung aus Schritt
c) , um Oxiluciferin freizusetzen und Lumineszenz zu emittieren;
e) Messen der emittierten Lumineszenz; und
f) Bestimmen der Konzentration des Pestizids in der Testprobe durch Vergleich der
gemessenen, emittierten Lumineszenz mit der Lumineszenz einer Vergleichsprobe.
2. Verfahren gemäß Anspruch 1, bei dem der Luciferinester von der folgenden Formel
ist:
worin R C&sub1;-C&sub6; Alkly oder Phenyl ist.
3. Verfahren gemäß Anspruch 2, wobei der Luciferinester D-Luciferinacetat ist.
4. Verfahren gemäß Anspruch 1, 2 oder 3, wobei das Gehirnmaterial von Bienen,
Schmeißfliegen, Hausfliegen, Seidenraupen oder anderen Gliederfüßern stammt.
5. Verfahren gemäß Anspruch 4, bei dem das Insektengehimmaterial ein
Gehirnhomogenisat aus Honigbienenköpfen umfasst.
6. Verfahren gemäß einem der Ansprüche 1 bis 5, wobei Schritt a) ein Inkubieren der
Testprobe und des Insektengehirnmaterials für 2 bis 10 Minuten umfasst.
7. Verfahren gemäß einem der vorhergehenden Ansprüche, wobei Schritt c) ein
Inkubieren der D-Luciferinestermischung für 2 bis 5 Minuten umfasst.
8. Verfahren gemäß Anspruch 3, wobei die Konzentration des D-Luciferinacetats in
der hergestellten Mischung in Schritt b) 1 · 10&supmin;¹¹ m oder weniger ist.
9. Verfahren gemäß einem der vorhergehenden Ansprüche, bei dem das Pestizid
ausgewählt ist aus Methomyl, Propoxur, Carbofuran, Bendocarb, Mevinphos,
Ethion, Chlorpyrifos, Phorat, Malathion, Oxidemeton-Methyl, Disulfoton, Methylparathion,
DDVP, Naled und Diazanon.
10. Verfahren zur Bestimmung der Konzentration von Organophosphat- und
Carbamatpestiziden in einer Testprobe, wobei das Verfahren umfasst:
a) Inkubieren einer Testprobe und eines homogenisierten Insektengehirnmaterials,
das von Bienen, Fliegen oder Seidenraupen stammt;
b) Zugeben von D-Luciferinacetat zu der inkubierten Mischung;
c) Inkubieren der D-Luciferinacetatmischung zum Freisetzen von D-Luciferin;
d) Zugeben von Adenosintriphosphat und Luciferase zu der Mischung, um
Oxiluciferin freizusetzen und Lumineszenz zu emittieren;
e) Messen der emittierten Lumineszenz während eines definierten Zeitraumes; und
f) Bestimmen der Konzentration des Pestizids in der Testprobe durch Vergleich der
gemessenen, emittierten Lumineszenz mit der Lumineszenz einer Vergleichsprobe
oder einem Standard.
11. Testkit für die Biolumineszenzbestimmung der Konzentration von Organophosphat-
und Carbamatpestiziden in einer Testprobe, wobei das Testkit in Kombination
umfasst:
a) eine gegenüber dem Pestizid empfindliche Insektengehirnzubereitung;
b) einen 6-substituierten D-Luciferinester, dessen Hydrolyse durch das Pestizid
inhibiert wird, zur Zugabe und Inkubation mit einer inkubierten Testprobe und dem
Gehirnmaterial; und
c) Luciferase und Adenosintriphosphat für die Zugabe zu einer inkubierten 6-
substituierten D-Luciferinestermischung.
12. Testkit gemäß Anspruch 11, enthaltend:
a) Inkubationsmittel um zunächst die Testprobe mit dem Gehimmaterial und später
die Testprobe und Gehirmaterial mit dem 6-substituierten D-Luciferinester zu
inkubieren;
b) Mittel zur Messung der emittierten Lumineszenz; und
c) Vergleichsmittel zum Vergleich mit der gemessenen, emittierten Lumineszenz
zur Bestimmung der Konzentration des Pestizids in der Testprobe.
13. Testkit gemäß Anspruch 11 oder 12, wobei der 6-substituierte D-Luciferinester D-
Luciferinacetat ist.
14. Testkit gemäß Anspruch 11, 12 oder 13, worin das Gehimmaterial ein von Bienen,
Schmeißfliegen, Hausfliegen, Seidenraupen oder anderen Gliederfüßern
stammendes Gehirnhomogenisat ist.
15. Verfahren zur Herstellung eines Luciferinesters wie er in Anspruch 2 definiert ist,
wobei das Verfahren umfasst:
Umsetzen eines N-acylierten Imidazols der Fomel:
in einem flüssigen Lösungsmittel, worin R C&sub1;-C&sub6; Alkyl oder Phenyl ist, mit D-
Luciferin, um den Luciferinester und Imidazol bereitzustellen.
16. Verfahren gemäß Anspruch 15, wobei das N-acylierte Imidazol N-Acetylimidazol ist
und der Luciferinester D-Luciferinacetat.
17. Verfahren gemäß Anspruch 16, wobei die Vollständigkeit der Umsetzung durch die
Abnahme der Biolumineszenz mit dem Fortschreiten der Umsetzung überwacht
wird.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/818,782 US5283180A (en) | 1990-07-19 | 1992-01-09 | Bioluminescence method for the determination of pesticides |
| PCT/US1993/000436 WO1993014222A1 (en) | 1992-01-09 | 1993-01-07 | Test kit and method for the determination of pesticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69330077D1 DE69330077D1 (de) | 2001-05-10 |
| DE69330077T2 true DE69330077T2 (de) | 2001-07-19 |
Family
ID=25226398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69330077T Expired - Fee Related DE69330077T2 (de) | 1992-01-09 | 1993-01-07 | Testsatz und verfahren zur bestimmung von pestiziden |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5283180A (de) |
| EP (1) | EP0576667B1 (de) |
| JP (1) | JPH06505880A (de) |
| AU (1) | AU667518B2 (de) |
| CA (1) | CA2105770C (de) |
| DE (1) | DE69330077T2 (de) |
| WO (1) | WO1993014222A1 (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5283180A (en) * | 1990-07-19 | 1994-02-01 | Charm Sciences, Inc. | Bioluminescence method for the determination of pesticides |
| GB9310238D0 (en) * | 1993-05-18 | 1993-07-14 | Mini Agriculture & Fisheries | Method,agents and kits for detection of organic agents |
| US5827675A (en) * | 1995-07-12 | 1998-10-27 | Charm Sciences, Inc. | Test apparatus, system and method for the detection of test samples |
| US7268229B2 (en) * | 2001-11-02 | 2007-09-11 | Promega Corporation | Compounds to co-localize luminophores with luminescent proteins |
| US20040044063A1 (en) * | 2002-05-31 | 2004-03-04 | Brent Stockwell | SMA therapy and cell based assay for identifying therapies |
| JP2004089117A (ja) | 2002-09-03 | 2004-03-25 | Toyo B-Net Co Ltd | ルシフェラーゼ検出試薬キット及び当該キットを使用したルシフェラーゼ検出方法 |
| AU2003267245C1 (en) * | 2002-09-20 | 2008-05-29 | Promega Corporation | Luminescence-based methods and probes for measuring cytochrome P450 activity |
| US7132249B1 (en) | 2003-05-12 | 2006-11-07 | Charm Sciences, Inc. | Method of determining allergenic food on surfaces |
| US7494781B1 (en) | 2003-05-12 | 2009-02-24 | Charm Sciences, Inc. | Sensitive method for detecting low levels of ATP |
| EP2272973B1 (de) * | 2005-05-31 | 2015-05-27 | Promega Corporation | Luminogene und fluorogene Verbindungen und Verfahren für den Nachweis von Molekülen oder Leiden |
| EP2092076A4 (de) * | 2006-11-13 | 2011-01-05 | Ateris Technologies Llc | Biomarker für pestizide |
| US20110166043A1 (en) * | 2007-11-14 | 2011-07-07 | Jon Owen Nagy | Biomarker detection-2 |
| US8288559B2 (en) * | 2008-08-18 | 2012-10-16 | Promega Corporation | Luminogenic compounds and methods to detect cytochrome P450 3A enzymes |
| CN103323415B (zh) * | 2013-07-01 | 2015-08-05 | 广州市酒类检测中心 | 一种检测氨基甲酸酯类的酶抑制法 |
| CN103389301A (zh) * | 2013-08-01 | 2013-11-13 | 辛焕发 | 一种农药残留的快速检测方法 |
| WO2015116867A1 (en) | 2014-01-29 | 2015-08-06 | Promega Corporation | Quinone-masked probes as labeling reagents for cell uptake measurements |
| CN111272726B (zh) * | 2020-05-08 | 2021-03-09 | 北京中检葆泰生物技术有限公司 | 一种检测食品中农药残留的方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408259A (en) * | 1966-01-21 | 1968-10-29 | Inst Mitchforschung Oranienbur | Process for detecting staphylococci-enterotoxin in foodstuffs |
| US4014745A (en) * | 1975-04-30 | 1977-03-29 | Nasa | Application of luciferase assay for ATP to antimicrobial drug susceptibility |
| SE428379B (sv) * | 1978-05-31 | 1983-06-27 | Lkb Produkter Ab | Bioluminiscens bestemning av atp och reagens herfor |
| US4238472A (en) * | 1978-11-27 | 1980-12-09 | United States Of America | Radioimmunoassay for chlorinated dibenzo-p-dioxins |
| DE2908054A1 (de) * | 1979-03-02 | 1980-09-11 | Boehringer Mannheim Gmbh | Verfahren und reagenz zur bestimmung der creatinkinase |
| US4469795A (en) * | 1981-08-26 | 1984-09-04 | Edward Ginns | Radioassay for monosialoglycosphingolipid (GM1) ganglioside concentration |
| US4520112A (en) * | 1983-03-09 | 1985-05-28 | The Johns Hopkins University | Assay method for organic calcium antagonist drugs and a kit for such an assay |
| US4665022A (en) * | 1984-02-17 | 1987-05-12 | The Regents Of The University Of California | Bioluminescent assay reagent and method |
| DE3537877A1 (de) * | 1985-10-24 | 1987-04-30 | Geiger Reinhard | Luciferin-derivate und immunoassays unter einsatz derartiger luciferin-derivate |
| US4925664A (en) * | 1986-10-20 | 1990-05-15 | University Of Utah | Spider toxins and methods for their use as blockers of calcium channels and amino acid receptor function |
| US5064657A (en) * | 1986-10-20 | 1991-11-12 | University Of Utah | Spider toxins and methods for their use as blockers of amino acid receptor function |
| DE3833628A1 (de) * | 1988-10-03 | 1990-04-12 | Genlux Forschungsgesellschaft | Verfahren zum nachweis und zur identifikation toxischer substanzen mit hilfe klonierter mikroorganismen |
| US5283180A (en) * | 1990-07-19 | 1994-02-01 | Charm Sciences, Inc. | Bioluminescence method for the determination of pesticides |
| US5200311A (en) * | 1990-07-19 | 1993-04-06 | Charm Sciences Inc. | Method of determination of pesticides by radiobiochemistry |
-
1992
- 1992-01-09 US US07/818,782 patent/US5283180A/en not_active Expired - Fee Related
-
1993
- 1993-01-07 DE DE69330077T patent/DE69330077T2/de not_active Expired - Fee Related
- 1993-01-07 JP JP5512696A patent/JPH06505880A/ja active Pending
- 1993-01-07 CA CA002105770A patent/CA2105770C/en not_active Expired - Fee Related
- 1993-01-07 AU AU35846/93A patent/AU667518B2/en not_active Ceased
- 1993-01-07 WO PCT/US1993/000436 patent/WO1993014222A1/en not_active Ceased
- 1993-01-07 EP EP93904519A patent/EP0576667B1/de not_active Expired - Lifetime
- 1993-09-23 US US08/125,935 patent/US5374535A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0576667A1 (de) | 1994-01-05 |
| EP0576667B1 (de) | 2001-04-04 |
| CA2105770A1 (en) | 1993-07-10 |
| DE69330077D1 (de) | 2001-05-10 |
| US5374535A (en) | 1994-12-20 |
| US5283180A (en) | 1994-02-01 |
| WO1993014222A1 (en) | 1993-07-22 |
| AU667518B2 (en) | 1996-03-28 |
| AU3584693A (en) | 1993-08-03 |
| JPH06505880A (ja) | 1994-07-07 |
| CA2105770C (en) | 1998-09-22 |
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